Acids such as anthranilic acid have been anchored to polymers in the past. Examples of these are the anchoring of anthranilic acid to polystyrene which is disclosed in U.S. Pat. Nos. 4,313,018 and 4,238,358. In this prior art process cross-linked polystyrene polymers or beads are first chloromethylated and then anthranilic acid is anchored to the chloromethylated polymer thereof by means of stirring an excess of the acid in the presence of a solvent.
U.S. Pat. No. 4,672,051 disclosed a polymer-bound dehydration catalyst for the conversion of aldehydes to olefins, where the polymer may be divinyl benzene cross-linked polystyrenes. The catalyst is prepared by chloromethylating the divinyl benzene cross-linked macroporous polystyrenes and then reacting the resulting polymer with a suitable reactant.
A polymer bound co-catalyst system useful for reductive alkylation is disclosed in U.S. Pat. No. 4,463,191. This system is a polymer-bound anthranilic acid palladium complex which is used as a catalyst system in conjunction with a sulfonic acid resin also bound thereto. The anthranilic acid polymer complex is prepared by first reacting anthranilic acid with a sytrene/vinyl-benzyl chloride/divinyl benzene resin in an organic solvent at 75.degree. C. for 18 hours, the product is then dried and thereafter reacted with a palladium salt in a dimethylformamide solvent system to obtain the product polymer.
U.S. Pat. No. 4,666,526 disclosed azine pigments which are produced by a method which consists of reacting isatoic anhydride or anthranilic acid esters or amides with an indole derivative. The polymers may be of natural origin such as rubber obtained by chemical modification such as cellulose or viscose, or they may be synthetically produced such as polymers, polyadducts or polycondensated polymers. Examples given by this patent are plastic materials such as polyvinyl chloride, polyvinyl acetate, polyvinyl propionate, polyolefins such as polyethylene or polyamides, superpolyamides, polymers and copolymers of acrylates, methacrylates, acrylonitrile, acrylamide, butadiene and styrene, and polyurethanes and polycarbonates.
Most of the prior art processes are in general complex, and produce by-products which must be separated from the desired ester or amide bridged polymeric product. In addition, the various processes also require elaborate equipment, in many instances involving two or more reaction vessels and are expensive to operate.
Accordingly, there is a need for a simpler, more efficient method of synthesizing pendant ester or amide bridged polymers which preserves the structure of the acid or amide, does not result in waste or by-products and does not require elaborate equipment.